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One of the oldest automobile brands celebrates its anniversary today. Formed from the remnants of the Henry Ford Company, the Cadillac Automobile Company was founded 110 years ago on August 22, 1902 by Henry Leland. Since the beginning, Cadillacs have always been extravagant, and as the brand attempts to regain its position as standard of the world, we’re crowning the five coolest Caddies ever designed.

1937 Cadillac Phaeton model 5859 — Look up classic beauty in the dictionary, and you’ll see an image of the custom-built 1937 Cadillac Fleetwood V-16 shown here. The Phaeton model 5859 was built by coachbuilder Fran Roxas who relied on the original blueprints of Cadillac designer John Hampshire. The original sketches of the powerful V-16 car served as inspiration for the Ciel concept car.

1949 Cadillac — The 1949 Cadillac was a major step forward for the company, as the outgoing car’s ancient L-head V-8 was replaced by a flathead V-8 that put out 10 more horsepower (160 versus 150). The new engine was about 200 pounds lighter, revved higher, and got better fuel mileage. The Cadillac was also named as Motor Trend’s very first car of the year.

1959 Cadillac Eldorado — This beauty incorporated new styling, with sharp and massive tailfins that have gone down in automotive history. Its twin-bullet taillights, and jewel-like grille added to its appeal, and let’s not forget its name translates to “the golden one” in Spanish.

Cadillac Cielconcept — The Cadillac Ciel is just a concept, but it’s still one of the most gorgeous cars we’ve ever seen wearing the brand’s logo. The Ciel concept stunned spectators last year at Pebble Beach with its effortless combination of strong retro themes with Cadillac’s current design language. The four-door convertible wears rear-hinged “suicide” doors, and is powered by a twin-turbocharged 3.6 liter V-6 mated to a hybrid all-wheel-drive drivetrain producing an estimated 425 hp and 430 lb-ft of torque.

Cadillac CTS-V (second generation) — Where do we even begin? The CTS-V is fast, has a wonderfully composed chassis, and looks like a million bucks on the road. How do we know? We had a CTS-V wagon in our long-term garage for a year, and nearly everyone who got seat time with the beast fell in love.